Potassium Phosphate, Tribasic → 3-Cyclopropyl-4-fluoroaniline

HRID 19791

反応式

HRID 19791 の反応式
Br[C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH:10]1(B(O)O)[CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:10]1([C:2]2[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=2[F:8])[CH2:12][CH2:11]1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 27792863-Bromo-4-fluoroaniline

生成物 1

HCID 574163033-Cyclopropyl-4-fluoroaniline収率 64%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-bromo-4-fluorophenylamine (synthesized as described in J. Org. Chem. 1981, 46, 2280-2286) (415 mg, 2.18 mmol), cyclopropyl boronic acid (244 mg, 2.84 mmol), potassium phosphate (1.62 g, 7.64 mmol), and tricyclohexyl phosphine (61 mg, 0.22 mmol) in toluene (10 ml) and water (0.5 ml) was added palladium acetate (25 mg, 0.11 mmol) and the reaction mixture was heated to 100° C. overnight. The mixture was then cooled to RT and diluted with water and extracted with ether. The organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 3-cyclopropyl-4-fluorophenylamine (210 mg, 64%). MS (ISP) 152.2 (M+H)+.

後処理

  1. temperatureThe mixture was then cooled to RT
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue which
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-14b57bd0666e45aab253ce6c60b843fa
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

関連ノート

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